Chemical Identity and Properties

6-Chloro-2-ethoxypyrimidin-4-amine (SKU: C192759) is a substituted pyrimidine bearing three key substituents: a chloro group at the 6-position, an ethoxy group at the 2-position, and an amino group at the 4-position. Its molecular formula is C₆H₈ClN₃O with a molecular weight of approximately 173.60 g/mol.

The compound is a solid at room temperature and is typically pale yellow to off-white in appearance. The simultaneous presence of a nucleophilic primary amine and an electrophilic aryl chloride on the pyrimidine ring makes it a bifunctional building block capable of participating in both nucleophilic substitution and coupling reactions. The ethoxy group at the 2-position can also serve as a leaving group under appropriate conditions, further expanding its synthetic utility.

Solubility: the compound is generally soluble in common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and dichloromethane (DCM). Aqueous solubility is limited at neutral pH. Researchers should verify exact solubility experimentally under their specific assay conditions.

Storage, Handling and Safety Guidelines

Storage: Store 6-Chloro-2-ethoxypyrimidin-4-amine in a tightly sealed container in a cool (2–8 °C or as specified on the certificate of analysis), dry, and well-ventilated location, protected from light and moisture. Prolonged exposure to air, humidity, or elevated temperatures may compromise purity and reactivity.

Personal Protective Equipment (PPE): When handling this compound, wear appropriate PPE including nitrile gloves, a laboratory coat, and safety goggles. Work in a fume hood or well-ventilated area to avoid inhalation of dust or aerosols. Avoid contact with skin, eyes, and mucous membranes.

Waste Disposal: Dispose of waste in accordance with local, regional, and national regulations governing hazardous chemical waste. Do not pour into drains or the environment. Consult the Safety Data Sheet (SDS) for full hazard classification and emergency response information before use.

Stability: Under recommended storage conditions, the compound is expected to be stable. However, the aryl chloride moiety may be susceptible to hydrolysis under strongly acidic or basic aqueous conditions. Prepare solutions fresh when possible and store under inert atmosphere if long-term stability is required.

Synthetic Applications and Reaction Protocols

6-Chloro-2-ethoxypyrimidin-4-amine is a privileged heterocyclic intermediate in medicinal chemistry and process chemistry. Its reactivity profile enables several key synthetic transformations:

• Nucleophilic Aromatic Substitution (SNAr): The C-6 chloro substituent is activated toward SNAr reactions with amines, thiols, and alkoxides. Reactions are typically conducted in polar aprotic solvents (e.g., DMF, NMP, DMSO) at elevated temperatures (60–120 °C) in the presence of a suitable base (e.g., K₂CO₃, Et₃N, DIPEA). This allows selective introduction of diverse nucleophiles at the 6-position to furnish 2-ethoxy-6-substituted-pyrimidin-4-amines.
• Transition-Metal-Catalyzed Cross-Coupling: The aryl chloride can participate in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig amination, and Negishi couplings, enabling access to biaryl and diarylamino pyrimidine derivatives relevant to kinase inhibitor programs.
• Ethoxy Group Displacement: Under harsh acidic or nucleophilic conditions, the 2-ethoxy group can be displaced to generate 2-substituted pyrimidine analogs, providing an additional handle for library synthesis.
• Acylation/Sulfonylation of the 4-Amino Group: The primary amine at the 4-position can be selectively acylated or sulfonylated, offering routes to amide and sulfonamide derivatives with modulated physicochemical properties.

Researchers should optimize reaction conditions (catalyst loading, base, solvent, temperature, and time) for their specific substrates. Always conduct small-scale optimization reactions before scaling up.

Quality, Purity and Analytical Characterization

Aladdin Scientific supplies 6-Chloro-2-ethoxypyrimidin-4-amine (C192759) with a purity specification confirmed by high-performance liquid chromatography (HPLC). A Certificate of Analysis (CoA) accompanies each lot and should be consulted to confirm the purity grade, lot-specific data, and recommended storage conditions before use.

Recommended Analytical Methods for In-House Verification:

• HPLC-UV: Use a C18 reverse-phase column with an acetonitrile/water gradient to assess purity. Monitor at 254 nm or the compound's absorption maximum.
• ¹H NMR and ¹³C NMR: Confirm structural identity in deuterated solvents such as CDCl₃ or DMSO-d₆. Key signals include the aromatic/vinyl proton on the pyrimidine ring, NH₂ protons, and the OCH₂CH₃ ethoxy resonances.
• LC-MS: Verify molecular ion [M+H]⁺ consistent with MW = 173.60 g/mol.
• Melting Point: Determine and compare against literature values as an additional purity check.

If the compound has been stored for an extended period or shows visible changes (discoloration, clumping), re-characterize before use in critical experiments. Contact Aladdin Scientific technical support for batch-specific documentation or purity queries.

Regulatory and Procurement Information

Product Availability: 6-Chloro-2-ethoxypyrimidin-4-amine is available from Aladdin Scientific under SKU C192759. Please visit the product page or contact your regional Aladdin representative for current stock levels, available quantities, and pricing.

Intended Use: This product is supplied for research and development purposes only. It is not intended for use in diagnostic procedures, drug manufacturing, food, household, or cosmetic applications without appropriate regulatory authorization.

Export Controls and Regulatory Compliance: Customers are responsible for ensuring compliance with all applicable local, national, and international regulations governing the purchase, import, export, and use of this chemical. Verify whether import licenses or other documentation are required in your jurisdiction prior to ordering.

Returns and Quality Issues: If the product does not meet the stated specification, contact Aladdin Scientific customer service within the applicable return window with your order details and CoA. Refer to Aladdin's Returns and Refunds Policy for full terms.

SDS Availability: The Safety Data Sheet (SDS) for C192759 is available upon request and should be reviewed by all personnel handling this compound prior to use.